2-Methylbenzylidenemalonic acid → 2-[(2-methylphenyl)methyl]propanedioic Acid

HRID 1651715Notes

Reaction equation

HRID 1651715 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH:4]=[C:5]([C:9]([OH:11])=[O:10])[C:6]([OH:8])=[O:7]>CCOC(C)=O.CCO.[Pd]>[CH3:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][CH:5]([C:9]([OH:11])=[O:10])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 1

HCID 100588002-Methylbenzylidenemalonic acid

Product 1

HCID 27375462-[(2-methylphenyl)methyl]propanedioic Acid

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Hydrogenate the acid of Step 1 (24.3 g) in EtOAc (600 ml) and EtOH (100 ml) at 60 psi with 5% Pd/C (1.0 g). After 2 hr., filter and concentrate to obtain the title compound as a beige solid, m.p. 132°-5°.

Workup

  1. filtration, filter
  2. concentrationconcentrate

Sources & evidence

ORD record
ord-8493594692ab4cebad87ac581f5d85ed
Source dataset
uspto-grants-1990_05
Patent number
US04929641

Reaction notes

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